Acetone → 2-(5-Bromopyridin-2-yl)propan-2-ol

HRID 1047227Notes

Reaction equation

HRID 1047227 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C([Li])CCC.[CH3:14][C:15]([CH3:17])=[O:16]>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]([OH:16])([CH3:17])[CH3:14])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 154863922-(5-Bromopyridin-2-yl)propan-2-olYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,5-Dibromopyridine (1.04 g, 4.39 mmol) was dissolved in toluene (22 mL) in a 100 mL round-bottomed flask. The mixture was cooled to −78° C. n-Butyllithium (3.02 mL, 4.83 mmol) was added dropwise. The mixture was stirred 30 min, followed by the addition of acetone (2 mL). The mixture was stirred 40 min and then let warm to rt. The mixture was washed with ammonium chloride (5% aq, 50 mL), water (50 mL) and then brine (50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by Biotage (16% ethyl acetate in hexanes). Concentration of the desired fractions afforded the product (0.82 g, 3.78 mmol, 86% yield). MS (ESI) m/z 216.0 [M]+, 218.1 [M+2]+.

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred 40 min
  3. washThe mixture was washed with ammonium chloride (5% aq, 50 mL), water (50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by Biotage (16% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-38930c898a0a4c77a78221171179208e
Source dataset
uspto-grants-2013_10
Patent number
US08569494B2

Reaction notes

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